The episode takes place on Valentine's Day, and the wives of Springfield are jealous of the attention Apu gives to his wife Manjula.
[1] Following the home media release of The Simpsons: The Complete Tenth Season, the episode received generally positive reviews from critics.
The rest of Springfield's women become jealous from all the attention Manjula is receiving, and find their men to be cheapskates (including Maude Flanders).
At Moe's Tavern, Homer encourages several of Springfield's men that they have to prevent Apu and Manjula from reconciling to save their own relationships and marriages.
The episode's title was pitched by fellow Simpsons writer Ron Hauge, who based it on the T-shirt slogan I'm with stupid.
During the scene, both characters speak the language accurately, as both Hooks and Hank Azaria (the voice of Apu) were given a phonetic transcription of their lines.
[2] In their book Picturing South Asian Culture in English: Textual and Visual Representations, Tasleem Shakur and Karen D'Souza analyzed "I'm with Cupid" along with the season 9 episode "The Two Mrs. Nahasapeemapetilons".
They wrote: "In a Valentine's day episode, the message is clearly critically showing up the all-American men of Springfield for their lack of romance.
Again, Apu is not so much represented in his ethnicity, but presented in his critical otherness to both contemporary degenerativeness of American culture, specifically male identities and ironically (re)constructed idea of South Asianness.
While the scene was conceived in order to provide exposition, the sport was included because badminton is "very popular" in India, according to writer Ian Maxtone-Graham.
[9] In its original American broadcast on February 14, 1999, "I'm with Cupid" received a 7.7 rating, according to Nielsen Media Research, translating to approximately 7.7 million viewers.
Mike Scully, George Meyer, Ian Maxtone-Graham, Ron Hauge and Matt Selman participated in the DVD's audio commentary of the episode.
[13] Warren Martyn and Adrian Wood of I Can't Believe It's a Bigger and Better Updated Unofficial Simpsons Guide gave the episode a positive review as well, calling it "Very, very clever and funny," and wrote "it's executed stylishly and Homer wins in the end; entirely by default of course, but maybe that's his reward for not falling off the skywriting plane until the last minute!"
However, they also criticized the episode for being "a little tacky," writing "After all, how nice are these people who want to ruin Apu and Manjula's day just because they're scared of looking bad?
"[8] Writing for IGN, Robert Canning described "I'm with Cupid" as "very smart and very funny" and "a great episode representing one piece of Apu's journey."
He added "Yes that the show lacks any spark, as it throws out a reasonable number of laughs," and concluded his review by writing that "it seems a little stale and not one of the year’s better programs.